Pienza Villas - Best Villa Pienza 2026

A historic square with a prominent tower and statues.

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Our top choices for Pienza villas

1. Podere Manafiore - historical villa with swimming pool

Monticchiello

Caroline R.

A stone building with a tiled roof, a small porch, and a pathway leading to it.

2. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

San Quirico d'Orcia

includes taxes & fees

16 Sept - 17 Sept

A stone building with multiple rooms, surrounded by lush greenery and trees.

3. WPRELAIS BORGO VIGNALUNGA

Toscana

Jeremy F.

includes taxes & fees

24 Sept - 25 Sept

A courtyard with a pathway leading to a circular garden area, surrounded by trees and a building with a tiled roof.

4. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

Trequanda

includes taxes & fees

7 Oct - 8 Oct

A tree, a lamp post, and a clear blue pool with a view of distant mountains.

5. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

Torrita di Siena

includes taxes & fees

14 Sept - 15 Sept

A patio table with a patterned tablecloth, an umbrella, and metal chairs.

6. Villa Falco-Cignella Resort Apartments in Tuscany

Trequanda

includes taxes & fees

28 Sept - 29 Sept

A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

7. Il Poggio dell'Eremita

Sinalunga

Paul Q.

includes taxes & fees

15 Sept - 16 Sept

A patio with a table and chairs, a large umbrella, and a vase of flowers.

8. Villa Cielo- Cignella Resort Tuscany Accommodation

Trequanda

includes taxes & fees

23 Sept - 24 Sept

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Top Pienza Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Very warm and friendly service."

Hotel Corsignano

10/10 Excellent

"My husband and I had an absolutely wonderful experience at Hotel Corsignano. From beginning to end, the staff went above and beyond to make us feel welcome and cared for. When we arrived a little later than expected, they were genuinely concerned about us and even made sure to save a parking spot for us. That level of thoughtfulness and hospitality really stood out. The hotel was exceptionally clean and in a fantastic location, just a few steps from the historic center of Pienza. And the breakfast was wonderful, with plenty of delicious options to choose from. We truly felt welcomed and well taken care of throughout our stay. We would happily stay here again and highly recommend Hotel Corsignano!"

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Truly a stunning boutique hotel that sits in the perfect place within the walled village of Cortana, Really enjoyed my 3 nights here mid trip. The staff have been trained exceptionally well. Zero pretention, impeccable service. The calm ( so quiet), amenities such as the spa and pool area, the breakfast and restaurants, and staff ( mgt, Eleanora, Matteo, Spa leads), attention to details, views from my window, coupled with the energy of the hotel are stand outs. Do treat yourself to a couple massages or treatments. Very fair pricing, and after all the walking and travel, so worth it. I had a massage my first day and my last, that were sandwiched between two other stays in Tuscany, SO glad I did. Tips: Little micro laundry place right at the bottom of the hill that was perfect to do my laundry for my last leg of my vacation. Day trip to Arezzo was so easy and amazing. Attended mass at 6pm on Sunday at a beautiful church above Cortana at the highest elevation. Lovely. They even have a little gift shop in the church. And the first weekend of the month there is a massive antiques fair in the Grand Piazza. 500 vendors. Recommend. There are other stunning boutique hotels within Cortano. Honestly feel this is your best pick. In off seasons this hotel may consider becoming a school of sorts for family businesses in the area, to act as a training academy of sorts for younger generation family members to ensure success."

Castello di Velona Resort Thermal SPA & Winery

8/10 Good

"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, it definitely helped, and we appreciated how responsive and accommodating they were. The hotel itself is an old castle, and that alone makes staying here such a special experience. The property is beautiful, incredibly charming, and very well maintained. You simply can’t replicate the character, history, and ambiance that come with staying in a property like this. The setting and surroundings are beautiful. It was definitely one of those experiences that felt uniquely Italian and added something special to our trip. My only recommendation would be to visit when the temperatures aren’t quite as hot. Given the age and historic nature of the property, I can appreciate that modernizing certain things like the air conditioning may not be as straightforward as it would be in a newer hotel. During cooler weather, I imagine our experience would have been close to perfect. Overall, we really enjoyed our stay and are glad we had the opportunity to experience such a beautiful and unique property. I would absolutely recommend it, just perhaps not during the hottest part of the summer!"

Precise Tale Poggio Alla Sala

10/10 Excellent

"Incredible stay in a beautiful location. The staff were amazing and the hospitality was top tier. We will most definitely be back. The recommendations given were brilliant and the room was stunning along with the rest of the hotel. We didn’t dine in the restaurant but our breakfast each morning was also wonderful."

Find out more about Pienza

Pienza Villas information

Number of reviews	116
Accommodation	1425 Villas
Lowest Price	€84
Highest Price	€5,928

Frequently asked questions

How much do villas in Pienza cost?

Rates for villas in Pienza range between €84 and €5,928 per night. Whatever your budget, you're sure to find a place that fits the bill with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many villas are there in Pienza?

Pack your suitcase and pick from 1425 villas in Pienza. For a family escape, a getaway with pals or anything in between, Expedia will help you find the right place in just a click or two.

Why book your villa in Pienza with Expedia?

With Expedia, it's easy to find your dream villa in Pienza. Holidaying with the kids? Use our helpful filters to search for stays with amenities like WiFi and a pool. If you have a certain budget, select how much you'd like to spend and your preferred star rating. We'll help you find the right stay in tune with your taste and style.

How can I find cheap villas in Pienza?

An excellent way to track down cheap villas in Pienza is with Expedia's user-friendly filter tool. Narrow your search results by budget, star rating and amenities to find unbeatable rates in just a click or two.

What is there to do near my villa in Pienza?

Whatever you're interested in, Pienza has plenty to keep you going. Artemisia Gallery, Pienza Cathedral and Palazzo Comunale are on many visitors' sightseeing itineraries. Don't forget about Palazzo Piccolomini, Historic Centre of Pienza and Piazza Pio II either. With Expedia's hotel deals in Pienza, you can discover more neat attractions like these with the money you save.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pienza villas

1. Podere Manafiore - historical villa with swimming pool

2. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

3. WPRELAIS BORGO VIGNALUNGA

4. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

5. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

6. Villa Falco-Cignella Resort Apartments in Tuscany

7. Il Poggio dell'Eremita

8. Villa Cielo- Cignella Resort Tuscany Accommodation

9. Artisti del Cavallo Tourism

10. VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

11. '...a delicious farmhouse in the countryside where only the wind blows...'

12. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

13. Apartment In A Hotel "Villa Cielo" with Shared Pool, Private Terrace & Wi-Fi

14. Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi

15. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

16. Villa Aquila-Cignella Resort Acommodation Tuscany

17. Apartment In A Hotel "Villa Salvia" with Shared Pool, Private Terrace & Wi-Fi

18. Hotel Apartment "Villa Limone" with Shared Pool & Wi-Fi

19. Apartment In A Hotel "Villa Aquila" with Shared Pool, Private Terrace & Wi-Fi

Find holiday rentals that suit your style

Top Pienza Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

Hotel Corsignano

Monastero di Cortona Hotel & Spa

Tenuta Santo Pietro

Nuovo Etruria Resort

Castello di Velona Resort Thermal SPA & Winery

Fonteverde Thermal Spa Resort Tuscany

Precise Tale Poggio Alla Sala

Agriturismo Il Macchione

Find out more about Pienza

Pienza Villas information

Frequently asked questions

Search Villas in Pienza

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pienza villas

1. Podere Manafiore - historical villa with swimming pool

2. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

3. WPRELAIS BORGO VIGNALUNGA

4. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

5. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

6. Villa Falco-Cignella Resort Apartments in Tuscany

7. Il Poggio dell'Eremita

8. Villa Cielo- Cignella Resort Tuscany Accommodation

9. Artisti del Cavallo Tourism

10. VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

11. '...a delicious farmhouse in the countryside where only the wind blows...'

12. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

13. Apartment In A Hotel "Villa Cielo" with Shared Pool, Private Terrace & Wi-Fi

14. Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi

15. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

16. Villa Aquila-Cignella Resort Acommodation Tuscany

17. Apartment In A Hotel "Villa Salvia" with Shared Pool, Private Terrace & Wi-Fi

18. Hotel Apartment "Villa Limone" with Shared Pool & Wi-Fi

19. Apartment In A Hotel "Villa Aquila" with Shared Pool, Private Terrace & Wi-Fi

Find holiday rentals that suit your style

Top Pienza Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

Find out more about Pienza

Pienza Villas information

Frequently asked questions